


Stiles has a kink and Derek loves it

by lizlybear



Category: Teen Wolf (TV)
Genre: Alternate Universe - Office, Anal Sex, Barebacking, Bottom Stiles Stilinski, Crossdressing Kink, Deepthroating, Gay Sex, Lingerie, M/M, Male Slash, Office Sex, Oral Sex, Panties, Stiles wears lingerie to work and Derek loves it, Top Derek Hale, Top Derek Hale/Bottom Stiles Stilinski, Underwear Kink, Women's Underwear
Language: English
Status: Completed
Published: 2016-06-26
Updated: 2016-06-26
Packaged: 2018-07-18 09:13:12
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,863
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7308871
Author URL: https://archiveofourown.org/users/lizlybear/pseuds/lizlybear
Summary: <blockquote class="userstuff">
              <p>Stiles wears lingerie to work, basically office porn with a tiny plot.</p>
            </blockquote>





	Stiles has a kink and Derek loves it

Stiles stands in front of his closet. A few months back, just before Halloween, he discovered a kink by accident. He had a party and he ordered a huntsman costume online. They delivered the wrong costume and he got a sexy red riding hood costume instead of the huntsman costume he ordered. He had been curious, no shame in admitting that and before he knew it he tried on the red riding hood outfit complete with stockings and black lacy underwear. Turns out he really likes to wear lingerie and a few weeks later he decided to buy himself a pair that would actually fit. Since then he had bought four more pairs.  
  
He picks up the red satin lacy one and nods to himself, the red one always makes him feel sexy and confident.  
  
He pulls it on and revels in the soft feeling of the satin on his skin. He looks at the clock and sees he only has thirty minutes left before he has to leave for work and he still has to make breakfast.

  
  
*****

  
  
Stiles always feels as if people can see the fact that he is wearing lingerie on his face. Logically he knows that is impossible but every time someone looks at him he is certain they can see it. He kind of likes that.  
  
Stiles arrives at work and puts his things away before getting coffee. Waiting for the machine to finish he sees Derek coming in. Derek looks like a dark haired, muscled god and Stiles may or may not have a crush on him. But Derek is an sarcastic asshole who never let's Stiles forget that he spilled coffee on Derek way back when he started working for Hale & co. It started a quiet word war between them. Every day Derek finds a way to tell him he thinks Stiles is a clumsy idiot and Stiles always finds a way to give Derek a creative backhanded compliment. Push and pull, it is what they did.  
  
Derek is the CEO of the company together with his sister, Laura. They took over after a big scandal surrounding Peter Hale and money laundering. After a restart the company was doing better than ever. Derek and Laura don't always get along, every other week they have a shouting match. Which usually results in Cora, the youngest Hale sibling, coming in to yell some sense into them. Laura mingles with the employees and is well liked, Derek has a permanent scowl on his face and is more feared than liked.

  
  
*****

  
Stiles is chatting with Isaac when he gets an message asking him to deliver a case file he has been working on to Laura's office asap.

He knocks on Laura's office door and waits for her to call him in. He hears Laura’s clear voice telling him to enter. When he enters the office Laura and Derek are both there. Stiles didn’t expect Derek. He tries not to look at him and because of that he stumbles over a carpet edge and drops the file. Derek smirks at him and Stiles flushes red. He can’t help himself the bastard is beautiful and very fucking sexy when he smirks. He bends over to pick up the file and realises his mistake the moment he feels his shirt ride up. He immediately bends his knees and picks up the file, straightens and gives the file to Laura without looking at Derek even though he can feel Derek's gaze on his back.  
  
"Is that all?" Stiles asks.  
  
"Yes, thank you Stiles," Laura says absent mindedly, she is already reading the document.  
  
All Stiles can think off when he closes the door behind him is: Did Derek see it? And if he did how will he react? Holy fuck he is going to get fired for wearing lingerie to work! No wait they can’t do that. Stiles will fight him on that.

  
  
*****

  
After a week of constantly looking over his shoulder, Stiles tells himself that Derek didn’t see anything and he starts to relax. Another week passes and Stiles relaxes a bit further. He stopped wearing his lingerie to work after the unfortunate bend over incident but today he deems it safe enough and decides to wear his black satin panties to work. They make him feel dangerous and in control.  
  
Derek has been hanging around the coffee machine all week and it forced Stiles to get his coffee on the third floor. Yes, he is avoiding Derek. Yes, he is being a coward, he knows that perfectly well. But the third floor coffee machine doesn’t make the same coffee as the one on his own floor. So after Stiles convinces himself that Derek didn't see anything and that he needs to stop being paranoid he gets up and goes to get a coffee on his own floor.  
  
While he waits for his coffee someone clears their throat behind him. Stiles startles and turns around and sees Derek standing there. "Hello, Stiles"  Derek says and gives him a lopsided smile.

"Hi, uh hello I mean," Stiles says nervously.

"So, red looks good on you," Derek says.  
  
Stiles can feel himself turning beet red. Holy fuck! Derek did see it! He isn’t paranoid, he should have trusted his gut instinct and really the coffee on the third floor wasn’t _that_ bad. Hold on, that bastard has been waiting for Stiles to show up just to make a comment about his kink.  
  
"Okay first you can't fire me for wearing it to work and second it is perfectly normal for men to wear lingerie." Stiles says and mentally scolds himself when he hears the high pitch in his voice.  
  
Derek reaches behind Stiles to get a cup and whispers in his ear: "Are you wearing it now?"

Stiles looks at Derek and gives him a once over before nodding yes.

"Can I see?" Derek asks. Slowly Stiles nods yes again.

"Meet me in my office in 30 minutes," Derek says before walking away.

Stiles looks after him and thinks that maybe Derek isn’t as unreachable as Stiles makes him out to be.

  
  
*****

  
Stiles leaves his coffee and fast tracks to his desk, he sits down and takes a deep breath. He grabs a packet lube from his bag, stuffs it in his pocket and hurries to the bathroom. He was never a boy scout but he always likes to be prepared. He picks a stall at the end and locks the door. He doesn’t have long, so a minimal stretching will have to do. Stiles’s dick strains against the black satin of his panties. He is going to show Derek his panties. He is going to have sex with his CEO. Stiles makes no illusions about that, they are two consenting adults and fuck he wants it. He has wanted it for ages and this is his chance.

He drops his pants and panties and puts a foot on the toilet seat. He slicks his finger and slowly pushes it in. He works his finger in and out before slipping in a second finger. Fuck, that feels good. He moves his fingers at a fast pace and once the slide is easy he adds another finger. Stiles squeezes his eyes shut and takes a few deep breaths, too much too soon. He pulls them out and adds more lube. He slides them in again and makes short work of prepping himself further. He pulls his panties and trousers back up, washes his hands and walks towards the elevators.

 

*****

 

Stiles is standing in front of Derek’s office. If he goes in it will change everything. Ha _if_ ? There is no _if_ , he is going in and he is going to have hot steamy office sex. The kind you read or watch and shake your head at because it will never happen outside of porn.

He knocks and holds his breath. What if Derek changed his mind. But directly following that thought comes Derek’s voice telling him to enter. Stiles walks in and stands in front of the big sturdy looking desk. And yes he notices it looks sturdy because he wants to be bend over that monstrosity and have Derek fuck him until Stiles can’t remember his own name. He also notices a bottle of lube standing on the desk and he knows that all his dirty, sexy fantasies are about to become a reality.

Derek walks around the desk and leans back against it he looks at Stiles and gestures with his hand: “Well? What are you waiting for _Stiles_? Show me.”

Stiles huffs and slowly opens his pants. Stiles lets the fabric slide down and he steps out of them.

He lifts his shirt and gives Derek a filthy smile, “Like what you see?”

Derek makes a sound in the back of his throat and nods. “Lose the shirt and turn around”

Stiles does as requested and looks over his shoulder at Derek.

“Anything else? Or is this it?” Stiles asks.

Derek smirks and rubs his own dick through his pants. “I think I want you to suck my dick and then I am going to bend you over my desk and fuck you senseless, are you okay with that?”

Stiles turns around and slowly walks towards Derek "I am more than okay with that".

He drops to his knees and takes a deep breath. He opens Derek’s pants and pulls them down to mid thigh. He takes Derek’s dick out of his pants and he licks his lips. It is perfect, thick, no curve and at least eight inches. Stiles looks up at Derek and smiles at him, he thumbs the slit before he takes the head into his mouth. Stiles licks around it and savours the taste. Derek puts a hand in Stiles’s hair and grips it tightly.

Stiles decides to go in for the kill. He learned to deep throat last summer and it is a skill he is dying to show off. But he miscalculates, the dick he learned it on was a bit smaller, he chokes and has to back off. _Way to be sexy,_ Stiles thinks.

Derek strokes Stiles’s face and makes encouraging noises and Stiles starts again. Licking down to Derek’s balls and then back up again repeating it a few times before he feels confident enough to try again. He licks the head and tongues the slit, he lets Derek's dick slide over his tongue but doesn’t pull off completely. He hollows out his cheeks while he slides it down towards his throat and he repeats the motion until he feels ready. He bobs his head down but this time he doesn’t stop until his nose is buried in the dark curly hair at the base. He feels Derek’s dick jump when he swallows around the head. Stiles fondles Derek’s balls and feels them tighten up. The grip in his hair gets painful when Derek urges him off.

“No, I want to be in you when I cum,” Derek says in a low, wrecked voice.

“You were in me, you giant douche,” Stiles murmurs.

Derek pulls Stiles to his feet and kisses him for the first time. Their lips connect and Derek licks Stiles’s bottom lip. Stiles is all too happy to open his mouth, the moment their tongues touch the kiss turns frantic. Stiles’s hands find their way into Derek’s perfect hair and Derek’s hands find their way to Stiles’s satin clad bottom. Derek groans and pulls Stiles tight against him. Stiles is pretty sure the satin is soaking through. He can feel Derek’s dick slide against him and with only a flimsy barrier it makes his hole clench and his dick leak. One of Derek’s hands is now inside the panties and Stiles can feel Derek’s finger circling his hole before he pushes it in. Derek makes a surprise noise and breaks the kiss. Stiles is panting and flushed.

Derek takes a deep breath and asks, “How many?”

Stiles knows what he means immediately and answers; “Three”

Derek kisses him again and adds another finger. When Derek adds a third finger Stiles moans and breaks the kiss, “I am ready, please just fuck me already!”

Derek pulls his fingers free and Stiles makes to pull his panties off but Derek stalls his hand and shakes his head, “Keep them on.” Derek lifts Stiles into his arms and turns towards the desk, he lays Stiles down on his back and kisses him hard while he pulls the panties down just enough to expose Stiles’s hole. Derek leans back and looks down at Stiles, he kisses him and then licks his way down Stiles’s chest moving towards his straining dick.

Derek fingers Stiles’s exposed hole while he mouths at his satin clad dick. He grabs the lube and puts a generous amount on his hand. Derek starts to stroke his own dick and Stiles can feel Derek’s fist touch his arse on every outward stroke.

“Are you ready?” Derek asks.

“I have been ready since I walked in. Get on with it, you tease!” Stiles growls.

Derek pulls his bottom towards the edge of the desk and positions his dick at Stiles’s relaxed and dripping hole. Stiles groans and tries to urge Derek on but Derek isn’t having it. “Grab the desk Stiles, keep your hands there and don’t cum until I tell you to cum. Think you can do that for me?” Stiles nods and grabs the desk.

Derek looks at him and then slams forward. The thrust makes the desk creak.

Derek pulls almost all the way out and slams back in. Stiles can’t catch his breath and it comes out almost stuttering, it hurts and it feels fantastic at the same time. Derek pushes Stiles’s legs towards his chest and looks down, he can see Stiles's dick straining against the satin and he can feel the edge of the panties chafing against his dick. It makes him go harder and faster, he doesn’t ease up and keeps Stiles right there on the edge with him.

After what seems like forever Derek pulls out and turns Stiles around. He thrusts back in, the second thrust and Derek manages to hit Stiles’s prostate. Stiles moans, he feels so fucking full, he grips the desk tighter and he tries to move with the powerful thrusts and the brutal pace. He tightens his muscles every time Derek pulls back and it seems to work because Derek’s thrusts become erratic. Derek can feel his balls tighten so he pulls Stiles up and wraps his hand around Stiles’s dick and squeezes.

“You can cum.” Almost immediately Stiles’s hole clenches up while his dick erupts a hot mess over Derek's hand. Derek pushes all the way in and cums with a grunt.

Derek pulls out, turns Stiles around and kisses him. It is a slow and sweet kiss that lasts until Stiles starts squirming. Stiles can feel Derek’s cum dripping out despite the fact that he is clenching hard to keep it in. Derek kisses down Stiles’s neck and slips two fingers into the abused hole. Over sensitive Stiles tries to pull away but Derek shushes him, “Let me, please.” Derek whispers into Stiles’s mouth. After a while Derek pulls away and leans his forehead against Stiles’s forehead, he removes his fingers with a soft pop. He grabs a chair and sits down heavily, his shirt clings to his body and there is a lube cum stain on his trousers. He looks at Stiles, when he sees the cum stained panties his dick gives a valiant try but can’t get hard again. Stiles looks like a wreck and fuck, if that isn’t a good look on him.

Suddenly Stiles starts laughing. “You’re still completely dressed! And holy fuck did we lock the door? Does your office even have a lock? Is this going to be awkward? Was this a one time thing? Because to be honest I would very much like a repeat performance, not right now obviously I mean I am not a teenager any more. Did I tell you I ramble when I get nervous? You can stop me any time. Don’t look so smug, you dick!”

Derek takes a breath. “No, we didn’t lock the door. Yes, this office has a lock. No, it won’t be awkward. Not a one time thing, I want a repeat performance as well. If I look smug it’s because I have reason to be.”

“Fine, so do you want to go and have an early dinner at my place?” Stiles says before he chickens out.

 

*****

 

And if Derek buys Stiles six pairs of men’s lingerie well nobody has to know about it.

And if Stiles buys a chastity device, it is because it was on sale and not because he wants to try out a new kink.

And if Derek really likes to put Stiles in said chastity device because he is a possessive bastard well that is nobody’s business anyway.

And if Derek buys a set of handcuffs then it is because Stiles can’t keep his hands to himself and not because of a recently discovered kink.

“Shut up Stiles”

**Author's Note:**

> I wrote a Merthur story a while back but I could easily see Stiles and Derek in this setting as well so I revised the story placed it in present tense, changed the names and voilà a Sterek story. I realise I have a ship type, it shouldn't have been this easy to switch the names around. pfff Hope you enjoyed my recycled story! Please feel free to let me know what you think about it. :-D


End file.
